Naslov
Competition and selectivity in supramolecular synthesis: structural landscape around 1- (pyridylmethyl)-2, 20- biimidazoles

Autori
Gunawardana, C. A. ; Desper, J. ; Sinha, A. S. ; Đaković, Marijana ; Aakeroy, C. B.

Izvornik
FARADAY DISCUSSIONS (1359-6640) 203 (2017); 371-388

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
supramolecular synthesis, hydrogen bonding, molecular electrostatic potential

Sažetak
Three isomeric forms of 1-(pyridylmethyl)-2, 20-biimidazole, A1–A3, have been synthesized and subjected to systematic co-crystallizations with selected hydrogenand halogen-bond donors in order to explore the impact of electrostatics and geometry on the resulting supramolecular architectures. The solid-state supramolecular behavior of A1–A3 is largely consistent in halogen-bonded co-crystals. Only two types of primary interactions, the N– H/N/N/H–N homomeric hydrogen-bond interactions responsible for the pairing of biimidazole moieties and the I/N(pyridine) halogen bonds responsible for the co-crystal formation and structure extension, are present in these systems. The co-crystallizations with hydrogen- bond donors (carboxylic acids), however, lead to multiple possible structural outcomes because of the presence of the biimidazole–acid N–H/O]C/N/H–O heterosynthon that can compete with biimidazole–biimidazole N–H/N/N/H–N homosynthon. In addition, the somewhat unpredictable nature of proton transfer makes the hydrogen-bonded co-crystals structurally less consistent than their halogen-bonded counterparts.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA